2-(N-tert-Butoxycarbonylpiperidin-2-yl)ethyl methanesulfonate → tert-BUTOXYCARBONYL-2(R/S)-[2-(1H-IMIDAZOL-1-YL)ETHYL]PIPERIDINE

HRID 392503Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 392503
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][CH2:15]OS(C)(=O)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH:21]1[CH:25]=[CH:24][N:23]=[CH:22]1.[Na]>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][CH2:15][N:21]1[CH:25]=[CH:24][N:23]=[CH:22]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 230901662-(N-tert-Butoxycarbonylpiperidin-2-yl)ethyl methanesulfonateHCID 57373095Imidazole sodium

Produkt 1

HCID 23521542tert-BUTOXYCARBONYL-2(R/S)-[2-(1H-IMIDAZOL-1-YL)ETHYL]PIPERIDINEAusbeute 69 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

The title compound from Step B above (2.68 g, 8.72 mmoles) (crude product, prior to chromatography) was dissolved in anhydrous DMF (30 mL) and sodium imidazole (1.18 g, 13.1 mmoles) was added. The mixture was heated at 70° C. for 2 h and then evaporated to dryness. The product was directly chromatographed on silica gel using 1% (10% conc. NH4OH in methanol)-dichloromethane as the eluant to give the title compound (1.69 g, 69%): ESMS: m/z 280.1 (MH+); dH (CDCl3) 1.48 ppm (9H, s, CH3); dC (CDCl3) CH3: 28.5, 28.5, 28.5; CH2: 19.1, 25.5, 28.9, 31.8, ˜39.1, 44.3; CH: 48.1, 118.9, 129.5, 137.1; C: 80.1, carbonyl not visible.

Aufarbeitung

  1. customevaporated to dryness
  2. customThe product was directly chromatographed on silica gel using 1% (10% conc. NH4OH in methanol)-dichloromethane as the eluant

Quellen und Nachweise

ORD-Eintrag
ord-06cec6602d824474b50d5a35adbad18b
Quelldatensatz
uspto-grants-2004_10
Patentnummer
US06800636B2

Notizen zur Reaktion

Wird geladen…